Dimethyl Sulfide → HCID 77230671, compound

HRID 2173187Notes

Reaction equation

HRID 2173187 reaction equation
[CH2:1]([C:4]1[CH:13]=[CH:12][C:7]2[C:8](=[O:11])[O:9][CH2:10][C:6]=2[C:5]=1[Br:14])[CH:2]=C.[O:15]=[O+][O-].CSC>CO.CCOC(C)=O>[Br:14][C:5]1[C:6]2[CH2:10][O:9][C:8](=[O:11])[C:7]=2[CH:12]=[CH:13][C:4]=1[CH2:1][CH:2]=[O:15]

Participants

6

Reactant 3

HCID 1068Dimethyl SulfideHCID 24823OzoneHCID 67515767HCID 67515767, compound

Product 1

HCID 77230671HCID 77230671, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 5-allyl-4-bromo-2-benzofuran-1(3H)-one (120 mg, 0.47 mmol) in methanol (20 mL) was bubbled ozone at −78° C. until the solution turned light blue. Excess ozone was removed by bubbling nitrogen through, which was followed by addition of dimethyl sulfide (0.35 mL, 4.7 mmol). The reaction was allowed to warm to RT, diluted with EtOAc, washed with brine, adsorbed onto silica gel, and purified by MPLC. Removal of solvent gave rise to (4-bromo-1-oxo-1,3-dihydro-2-benzofuran-5-yl)acetaldehyde.

Workup

  1. customExcess ozone was removed
  2. customby bubbling nitrogen through, which
  3. washwashed with brine
  4. custompurified by MPLC
  5. customRemoval of solvent

Sources & evidence

ORD record
ord-7092debf2e1d4ba99f7f307af7294bc0
Source dataset
uspto-grants-2015_06
Patent number
US09056859B2

Reaction notes

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